Hemingway St, Winchester, MA Property Records

Middlesex County and Winchester Town property records for 43 addresses on Hemingway St, Winchester, MA · Last verified October 2026

Hemingway St Highlights

Properties 43
Median Sale Price $1,100,000
Deeds and Mortgages on File 69
Median Price per Sqft $479
Owner Occupied 79%
Median Annual Tax Bill $127
Median Year Built 1929
Median Ownership Tenure 10 years

Properties on Hemingway St

Owner names and prior sale amounts shown locked below are available instantly with a free trial.

8 Hemingway St

3 bd · 1 ba · 1,286 sqft · built 1900 · 0.23 acres

Last Sale Tax Bill Prior Sale Owner Records
$690,000Mar 2024 $7,7032026 Amount on Record May 2022 Owner on Record Assessor + 5 DocumentsUpdated Oct 2026

16 Hemingway St

3 bd · 2.5 ba · 1,766 sqft · built 1830 · 0.095 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,052,000Nov 2023 $11,2652026 Amount on Record Apr 2021 2 Owners on Record Owner Occupied Assessor + 5 DocumentsUpdated Oct 2026

18 Hemingway St

5 bd · 3.5 ba · 2,137 sqft · built 2015 · 0.057 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,280,000Jul 2025 $14,1402026 Amount on Record Aug 2016 2 Owners on Record Owner Occupied Assessor + 4 DocumentsUpdated Oct 2026

21 Hemingway St

3 bd · 2 ba · 2,212 sqft · built 2016 · 0.149 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,002,400Apr 2017 $15,0462026 Amount on Record Oct 2015 2 Owners on Record Owner Occupied Assessor + 2 DocumentsUpdated Oct 2026

22 Hemingway St

3 bd · 1.5 ba · 1,238 sqft · built 1915 · 0.09 acres

Last Sale Tax Bill Prior Sale Owner Records
$365,000Mar 2003 $10,0832026 2 Owners on Record Owner Occupied AssessorUpdated Oct 2026

25 Hemingway St

2 bd · 1.5 ba · 1,890 sqft · built 1969 · 0.15 acres

Last Sale Tax Bill Prior Sale Owner Records
$962,000Dec 2024 $9,7702026 2 Owners on Record Owner Occupied Assessor + 1 DocumentUpdated Oct 2026

26 Hemingway St

3 bd · 1.5 ba · 1,836 sqft · built 1890 · 0.097 acres

Last Sale Tax Bill Prior Sale Owner Records
$660,000Dec 2015 $10,6392026 Amount on Record Mar 2007 2 Owners on Record Owner Occupied Assessor + 2 DocumentsUpdated Oct 2026

28 Hemingway St

4 bd · 3.5 ba · 2,600 sqft · built 1900 · 0.096 acres

Last Sale Tax Bill Prior Sale Owner Records
$593,000Jul 2013 $13,3192026 Amount on Record Jan 2005 2 Owners on Record Owner Occupied Assessor + 1 DocumentUpdated Oct 2026

29 Hemingway St

4 bd · 1.5 ba · 1,528 sqft · built 1925 · 0.142 acres

Last Sale Tax Bill Prior Sale Owner Records
$465,000May 2010 $10,4682026 Amount on Record Dec 2002 2 Owners on Record Owner Occupied Assessor + 1 DocumentUpdated Oct 2026

32 Hemingway St

4 bd · 4 ba · 2,408 sqft · built 2010 · 0.15 acres

Last Sale Tax Bill Prior Sale Owner Records
$93,750Oct 1998 $15,6352026 2 Owners on Record Owner Occupied AssessorUpdated Oct 2026

33 Hemingway St

5 bd · 3.5 ba · 2,293 sqft · built 1925 · 0.134 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,100,000Oct 2020 $15,1692026 Amount on Record Dec 2015 2 Owners on Record Owner Occupied Assessor + 3 DocumentsUpdated Oct 2026

36 Hemingway St

4 bd · 3.5 ba · 4,091 sqft · built 2020 · 0.168 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,572,500Aug 2020 $20,1772026 Amount on Record Sep 2019 2 Owners on Record Owner Occupied Assessor + 2 DocumentsUpdated Oct 2026

37 Hemingway St

3 bd · 2.5 ba · 1,706 sqft · built 1925 · 0.136 acres

Last Sale Tax Bill Prior Sale Owner Records
$550,000Aug 2017 $10,4502026 Amount on Record Aug 2000 2 Owners on Record Owner Occupied Assessor + 2 DocumentsUpdated Oct 2026

41 Hemingway St

4 bd · 2.5 ba · 3,021 sqft · built 1984 · 0.139 acres

Last Sale Tax Bill Prior Sale Owner Records
$845,000Oct 2015 $13,0812026 Amount on Record Oct 2008 2 Owners on Record Owner Occupied Assessor + 1 DocumentUpdated Oct 2026

42 Hemingway St

3 bd · 1 ba · 1,654 sqft · built 1860 · 0.159 acres

Last Sale Tax Bill Prior Sale Owner Records
$10,3892026 Owner on Record Owner Occupied Assessor + 1 DocumentUpdated Oct 2026

45 Hemingway St

4 bd · 3 ba · 2,419 sqft · built 1956 · 0.185 acres

Last Sale Tax Bill Prior Sale Owner Records
$975,000Oct 2022 $11,5512026 Amount on Record Jul 2019 2 Owners on Record Owner Occupied Assessor + 7 DocumentsUpdated Oct 2026

47 Hemingway St

3 bd · 4.5 ba · 3,292 sqft · built 1956 · 0.202 acres

Last Sale Tax Bill Prior Sale Owner Records
$13,6422026 2 Owners on Record Owner Occupied AssessorUpdated Oct 2026

49 Hemingway St

3 bd · 1 ba · 1,512 sqft · built 1940 · 0.149 acres

Last Sale Tax Bill Prior Sale Owner Records
$10,6562026 Owner on Record Owner Occupied AssessorUpdated Oct 2026

54 Hemingway St

2 bd · 1.5 ba · 1,287 sqft · built 1900 · 0.106 acres

Last Sale Tax Bill Prior Sale Owner Records
$430,000Jun 2005 $9,9742026 Amount on Record Mar 2001 Owner on Record Owner Occupied Assessor + 2 DocumentsUpdated Oct 2026

55 Hemingway St, #57

6 bd · 2 ba · 2,760 sqft · built 1926 · 0.184 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,175,000Dec 2021 $13,0122026 —Jul 2006 2 Owners on Record Assessor + 1 DocumentUpdated Oct 2026

58 Hemingway St

3 bd · 1.5 ba · 1,392 sqft · built 1880 · 0.094 acres

Last Sale Tax Bill Prior Sale Owner Records
$9,8062026 2 Owners on Record Owner Occupied AssessorUpdated Oct 2026

59 Hemingway St, #61

4 bd · 2 ba · 2,808 sqft · built 1929 · 0.359 acres

Last Sale Tax Bill Prior Sale Owner Records
$13,6652026 Owner on Record Assessor + 1 DocumentUpdated Oct 2026

65 Hemingway St

3 bd · 2 ba · 2,100 sqft · built 1924 · 0.266 acres

Last Sale Tax Bill Prior Sale Owner Records
$132,000Jul 1993 $11,4932026 Amount on Record Nov 1992 2 Owners on Record Owner Occupied AssessorUpdated Oct 2026

67 Hemingway St, #69

5 bd · 3.5 ba · 2,918 sqft · built 1831 · 0.514 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,100,000Apr 2025 $16,0212026 Amount on Record Oct 2014 Owner on Record Assessor + 8 DocumentsUpdated Oct 2026

68 Hemingway St

2 bd · 2 ba · 1,943 sqft · built 1928 · 0.16 acres

Last Sale Tax Bill Prior Sale Owner Records
$6,3722026 Owner on Record Owner Occupied Assessor + 1 DocumentUpdated Oct 2026

70 Hemingway St

2 bd · 1 ba · 1,044 sqft · built 1928 · 0.197 acres

Last Sale Tax Bill Prior Sale Owner Records
$270,000Feb 2013 $4,2492026 Amount on Record Sep 1996 2 Owners on Record Owner Occupied Assessor + 2 DocumentsUpdated Oct 2026

74 Hemingway St

3 bd · 2.5 ba · 1,402 sqft · built 1935 · 0.112 acres

Last Sale Tax Bill Prior Sale Owner Records
$30,000Dec 1977 $10,1072026 2 Owners on Record Owner Occupied Assessor + 1 DocumentUpdated Oct 2026

75 Hemingway St

20 bd · 19 ba · 19,891 sqft · built 1962 · 1.74 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,823,334Dec 2010 $59,0262026 Amount on Record Nov 1998 Owner on Record Assessor + 1 DocumentUpdated Oct 2026

76 Hemingway St

4 bd · 2.5 ba · 2,675 sqft · built 2015

Last Sale Tax Bill Prior Sale Owner Records
$13,1132026 2 Owners on Record Owner Occupied Assessor + 2 DocumentsUpdated Oct 2026
Last Sale Tax Bill Prior Sale Owner Records
$939,500Jul 2016 2 Owners on Record AssessorUpdated Jun 2023

78 Hemingway St

4 bd · 2.5 ba · 2,675 sqft · built 2015

Last Sale Tax Bill Prior Sale Owner Records
$13,0512026 Owner on Record Owner Occupied Assessor + 1 DocumentUpdated Oct 2026

79 Hemingway St

3 bd · 4.5 ba · 2,446 sqft · built 1915 · 0.297 acres

Last Sale Tax Bill Prior Sale Owner Records
$13,5752026 2 Owners on Record Owner Occupied AssessorUpdated Oct 2026

82 Hemingway St, #84

4 bd · 2 ba · 1,872 sqft · built 1910 · 0.121 acres

Last Sale Tax Bill Prior Sale Owner Records
$11,0742026 Owner on Record Owner Occupied Assessor + 3 DocumentsUpdated Oct 2026

87 Hemingway St, #1

4 bd · 3.5 ba · 3,079 sqft · built 2015

Last Sale Tax Bill Prior Sale Owner Records
$1,049,000Jan 2017 $16,1272026 2 Owners on Record Owner Occupied Assessor + 1 DocumentUpdated Oct 2026

87 Hemingway St, #2

4 bd · 3.5 ba · 3,087 sqft · built 2015

Last Sale Tax Bill Prior Sale Owner Records
$1,025,000Jan 2017 $16,1592026 2 Owners on Record Assessor + 1 DocumentUpdated Oct 2026

88 Hemingway St, #90

4 bd · 2 ba · 2,854 sqft · built 1910 · 0.14 acres

Last Sale Tax Bill Prior Sale Owner Records
$800,000Sep 2014 $13,5202026 Amount on Record Jan 2013 2 Owners on Record Owner Occupied AssessorUpdated Oct 2026

91 Hemingway St

3 bd · 4.5 ba · 3,470 sqft · built 2015

Last Sale Tax Bill Prior Sale Owner Records
$990,000Oct 2016 $15,2102026 2 Owners on Record Owner Occupied Assessor + 1 DocumentUpdated Oct 2026

95 Hemingway St

4 bd · 4.5 ba · 3,400 sqft · built 2015

Last Sale Tax Bill Prior Sale Owner Records
$995,000Nov 2020 $15,0082026 —Oct 2016 2 Owners on Record Owner Occupied Assessor + 2 DocumentsUpdated Oct 2026

96 Hemingway St

2 bd · 1 ba · 1,082 sqft · built 1900 · 0.23 acres

Last Sale Tax Bill Prior Sale Owner Records
$7,4132026 2 Owners on Record Owner Occupied Assessor + 2 DocumentsUpdated Oct 2026

99 Hemingway St

4 bd · 3.5 ba · 2,986 sqft · built 2014

Last Sale Tax Bill Prior Sale Owner Records
$1,030,000Jun 2015 $15,5552026 Amount on Record Jun 1988 2 Owners on Record Owner Occupied Assessor + 2 DocumentsUpdated Oct 2026
Last Sale Tax Bill Prior Sale Owner Records
$1,030,000Jun 2015 2 Owners on Record AssessorUpdated Jun 2023

101 Hemingway St

4 bd · 3.5 ba · 3,006 sqft · built 2014

Last Sale Tax Bill Prior Sale Owner Records
$991,875Jul 2015 $15,5412026 2 Owners on Record Owner Occupied AssessorUpdated Oct 2026
Last Sale Tax Bill Prior Sale Owner Records
$991,875Jul 2015 2 Owners on Record AssessorUpdated Jun 2023

Property Records in Nearby Streets